Herbicidal composition

ABSTRACT

The present invention provides for herbicidal composition comprising (i) 3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide, and (ii) ethyl 2-chloro-3-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindolin-2-yl)phenyl]acrylate as active ingredients. The present inventive composition can control a wide variety of weeds in corn fields, soybean fields, wheat fields, barley fields, oats fields, rye fields, rice fields, paddy fields or the like, with selectivity to crops. Methods for controlling weeds are also provided.

FIELD OF THE INVENTION

The present invention relates to a herbicidal composition.

BACKGROUND OF THE INVENTION

Currently, various herbicides are being utilized, but since there arevarious weeds that are targets of control, and because the growth ofweeds continues for a long time, a herbicide is desired that has ahigher herbicidal activity, a faster appearance of herbicidal effect, awider herbicidal spectrum and that is safe for crops.

SUMMARY OF THE INVENTION

The present inventor has intensely studied to seek out an excellentherbicide, and has found that by applying a herbicidal composition(hereinafter, referred to as the present inventive composition) whichcomprises, as active ingredients, (i)3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide (common name:bentazone, hereinafter, referred to as bentazone), and (ii) ethyl2-chloro-3-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindolin-2-yl)phenyl]acrylate(common name: cinidon-ethyl, hereinafter, referred to as cinidon-ethyl),various weeds that emerge or grow in crop-lands or non-crop-lands can becontrolled effectively, thereby completing the present invention. Thatis, since the herbicidal effect of the present inventive composition issynergistically increased as compared with the cases where the activeingredients are independently used, the amount used thereof can bereduced. By using the present inventive composition, the time necessaryfor appearance of a herbicidal effect can be shortened, and a broadenedweed control spectrum can be achieved synergistically, as compared withthe cases where the active ingredients are independently used. Moreover,a wide variety of weeds can be controlled selectively, without producingproblems of phytotoxicity against crops such as corn, soybean, wheat,barley, oats, rye and rice. In particular, when used in a corn field orsoybean field, the present composition is excellent for selectivity.Accordingly, the present invention has been obtained.

DETAILED DESCRIPTION OF THE INVENTION

The present invention provides a herbicidal composition that comprises,as active ingredients, (i) bentazone and (ii) cinidon-ethyl.

Bentazone is a compound described in Farm Chemicals Handbook, 1995(established by Meister Publishing Co., 1995) page C48 and the like.

Cinidon-ethyl is a compound described in JP 62-185071 A.

The present inventive herbicidal compositions are excellent asherbicides because they have a herbicidal activity against a widevariety of weeds with good selectivity between weeds and crops, and theyexhibit an excellent herbicidal activity in no-till cultivation andnon-agricultural fields as well as in till cultivation.

The present inventive herbicidal compositions have a herbicidal activityagainst the following variations of weeds that cause problems for cropsin fields of corn, soybean, wheat, barley, oats, rye or rice.

Polygonaceous weeds:

wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonumlapathifolium), pennsylvania smartweed (Polygonum pensylvanicum),ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleaf dock (Rumex obtusifolius) and Japanese knotweed (Polygonumcuspidatum);

Portulacaceous weeds:

common purslane (Portulaca oleracea);

Caryophyllaceous weeds:

common chickweed (Stellaria media);

Chenopodiaceous weeds:

common lambsquarters (Chenopodium album) and kochia (Kochia scoparia)

Amaranthaceous weeds:

redroot pigweed (Amaranthus retroflexus) and smooth pigweed (Amaranthushybridus);

Cruciferous (brassicaceous) weeds:

wild radish (Raphanus raphabistrum), wild mustard (Sinapis arvensis) andShepherds purse (Capsella bursa-pastoris);

Leguminous (fabaceous) weeds:

hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia),Florida beggarweed (Desmodium tortuosum), and white clover (Trifoliumrepens);

Malvaceous weeds:

velvetleaf (Abutilon theophrasti) and prickly sida (Sida spinosa);

Violaceous weeds:

field pansy (Viola arvensis) and wild pansy (Viola tricolor);

Rubiaceous weeds:

catchweed bedstraw (Galium aparine);

Convolvulaceous weeds:

ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoeapurpurea), entireleaf morningglory (Ipomoea hederacea var.integriuscula), pitted morningglory (Ipomoea lacunosa) and fieldbindweed (Convolvulus arvensis);

Labiate weeds:

red deadnettle (Lamium purpureum) and henbit (Lamium amplexicaure);

Solanaceous weeds:

jimsonweed (Datura stramonium) and black nightshade (Solanum nigrum);

Scrophulariaceous weeds:

Persian speedwell (Veronica persica) and Ivyleaf speedwell (Veronicahederifolia);

Composite weeds:

common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthusannuus), scentless chamomile (Matricaria perforata or inodora), cornmarigold (Chrysanthemum segetum), pineappleweed (Matricariamatricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed(Ambrosia trifida), Mare'stail (Erigeron canadensis), Artemisiaprinceps, Solidago altissima;

Boraginaceous weeds:

forget-me-not (Myosotis arvensis)

Asclepiadaceous weeds:

common milkweed (Asclepias syriaca)

Euphorbiaceous weeds:

sun spurge (Euphorbia helioscopia) and spotted spurge (Euphorbiamaculata)

Graminaceous weeds:

barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis),giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis),goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass(Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghumhalepense), quackgrass (Agropyron repens), downy brome (Bromustectorum), Bermudagrass (Cynodon dactylon), fall panicum (Panicumdichotomiflorum), Panicum texanum and shattercane (Sorghum vulgare);

Commelinaceous weeds:

common dayflower (Commelina communis)

Equisetaceous weeds:

field horsetail (Equisetum arvense);

Cyperaceous weeds:

rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus) andyellow nutsedge (Cyperus esculentus)

At the same time the present inventive composition exhibits nosignificant phytotoxicity on crops such as corn, soybean, wheat, barley,oats, rye and rice. In particular, when used in corn field or soybeanfield, the present composition is excellent for selectivity.

When the present inventive composition is used in paddy fields, it maybe sprayed to foliage of weeds in a preplant burndown application beforeflooding, or after seeding rice it may be sprayed to foliage of weeds ina delayed pre-emergence application before flooding, preferably.

The present composition effectively exhibits an excellent herbicidalactivity on weeds, e.g., dicotyledonous plants such as hemp sesbania(Sesbania exaltata), ivyleaf morningglory (Ipomoea hederacea), tallmorningglory (Pharbitis purpurea), entireleaf morningglory (Ipomoeahederacea var. integriuscula), pitted morningglory (Ipomoea lacunosaL.), common cocklebur (Xanthium pensylvanicum), and pensylvaniasmartweed (Polygonum pensylvanicum); and monocotyledonous plants such asbarnyardgrass (Echinochloa crus-galli), southern crabgrass (Digitariaciliaris), goosegrass (Eleusine indica), sprangletop (Leptochloachinensis), broadleaf signalgrass (Brachiaria platyphylla), umbrellasedge (Cyperus difformis), and rice flatsedge (cyperus iria), while itexhibits no significant phytotoxicity on rice.

For the present inventive composition, the mixing ratio of bentazone tocinidon-ethyl for active ingredients, may vary with the species of weedsto be controlled, the situation, conditions of application and the like,but is usually in the range from about 4:1 to 400:1 by weight,preferably, in the range of about 4:1 to 40:1 by weight.

The present inventive composition is usually utilized after formulatinginto emulsifiable concentrates, wettable powders, flowables, granules orthe like by mixing a solid carrier(s), liquid carrier(s), or the like,and when necessary, adding surfactant(s) or other adjuvants forformulation. The formulations thereof generally comprise bentazone andcinidon-ethyl in a total amount of about 0.5 to 90% by weight, andpreferably about 1 to 80% by weight.

In an event of formulation, as the utilized solid carrier or diluent,examples include fine powders or granules of clays (e.g., kaolinite,diatomaceous earth, synthetic hydrated silicon oxide, Fubasami clay,bentonite, acid clay), talc and other inorganic minerals (e.g.,sericite, powdered quartz, powdered sulfur, activated carbon, calciumcarbonate), and chemical fertilizers (e.g., ammonium sulfate, ammoniumphosphate, ammonium nitrate, ammonium chloride, urea); and as the liquidcarrier or diluent, examples include water, alcohols (e.g., methanol,ethanol), ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone),aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene,methylnaphthalene), non-aromatic hydrocarbons (e.g., hexane,cyclohexane, kerosine), esters (e.g., ethyl acetate, butyl acetate),nitriles (e.g., acetonitrile, isobutyronitrile), ethers (e.g., dioxane,diisopropyl ether), acid amides (e.g., dimethylformamide,dimethylacetamide), and halogenated hydrocarbons (e.g., dichloroethane,trichloroethylene).

As the surfactant, examples include alkylsulfic esters, alkylsulfonicsalts, alkylarylsulfonic salts, alkyl aryl ethers and theirpolyoxyethylene derivatives, polyethylene glycol ethers, polyhydricalcohol esters and sugar alcohol derivatives.

As the other adjuvants for formulation, examples include adhesive agentsor dispersing agents, such as casein, gelatin, polysaccharides (e.g.,starch, gum arabic, cellulose derivatives, alginic acid), ligninderivatives, bentonite, and synthetic water-soluble polymers (e.g.,polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid); andstabilizers such as PAP (isopropyl acid phosphate), BHT(2,6-tert-butyl-4-methylphenol), BHA (2-/3-tert-butyl-4-methoxyphenol),vegetable oils, mineral oils, fatty acids, and fatty acid esters.

The present inventive composition can also be prepared by formulatingeach of the active ingredients by a formulation methods as describedabove, and then mixing these formulations together.

The present inventive composition formulated in the above manner may beapplied to plants by itself (i.e., as it is) or with a dissolvingthereof in water. The present composition may further be utilized bymixing with other herbicide(s) to provide an enhancement in herbicidalactivity, and further they may be utilized in combination withinsecticides, bactericides, fungicides, plant growth regulators,fertilizers, safeners or soil conditioners.

The application amount of the present inventive composition may varywith the mixing rate of bentazone to cinidon-ethyl, weather conditions,formulation, application timing, application method, applicationlocation, objective weed to be controlled or objective crop to beprotected, but the total amount of the active ingredient compoundsapplied per 1 hectare is usually from about 50 to 5,000 g, andpreferably 200 to 2,000 g. Emulsifiable concentrates, wettable powders,flowables or the like are applied after diluting the predeterminedamount per 1 hectare with about 100 to 1000 L of water.

Hereinafter, the formulation examples are given. Parts represents partsby weight in the examples below.

FORMULATION EXAMPLE 1

Five parts of cinidon-ethyl, 25 parts of bentazone, 3 parts of calciumligninsulfonate, 2 parts of sodium laurylsulfate and 65 parts ofsynthetic hydrated silicon oxide are well pulverized and mixed to obtaina wettable powder.

FORMULATION EXAMPLE 2

0.4 Part of cinidon-ethyl, 40 parts of bentazone, 3 parts of calciumligninsulfonate, 2 parts of sodium laurylsulfate and 54.6 parts ofsynthetic hydrated silicon oxide are well pulverized and mixed to obtaina wettable powder.

FORMULATION EXAMPLE 3

0.5 Part of cinidon-ethyl, 25 parts of bentazone, 3 parts of calciumligninsulfonate, 2 parts of sodium laurylsulfate and 69.5 parts ofsynthetic hydrated silicon oxide are well pulverized and mixed to obtaina wettable powder.

FORMULATION EXAMPLE 4

0.5 Part of cinidon-ethyl, 10 parts of bentazone, 3 parts of calciumligninsulfonate, 2 parts of sodium laurylsulfate and 84.5 parts ofsynthetic hydrated silicon oxide are well pulverized and mixed to obtaina wettable powder.

FORMULATION EXAMPLE 5

Five parts of cinidon-ethyl, 25 parts of bentazone, 3 parts ofpolyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 64 parts of water are mixed and wet pulverized until theparticle size thereof is 5 microns or smaller, to thereby obtain aflowable.

FORMULATION EXAMPLE 6

0.4 Part of cinidon-ethyl, 40 parts of bentazone, 3 parts ofpolyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 53.6 parts of water are mixed and wet pulverized untilthe particle size thereof is 5 microns or smaller, to thereby obtain aflowable.

FORMULATION EXAMPLE 7

0.5 Part of cinidon-ethyl, 25 parts of bentazone, 3 parts ofpolyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 68.5 parts of water are mixed and wet pulverized untilthe particle size thereof is 5 microns or smaller, to thereby obtain aflowable.

FORMULATION EXAMPLE 8

0.5 Part of cinidon-ethyl, 10 parts of bentazone, 3 parts ofpolyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 83.5 parts of water are mixed and wet pulverized untilthe particle size thereof is 5 microns or smaller, to thereby obtain aflowable.

Hereinafter, the test examples are given. Evaluation Criteria Theherbicidal activity is evaluated at 11 levels with indices of 0 to 10,i.e., shown by numeral “0”, “1”, “2”, “3”, “4”, “5”, “6”, “7”, “8”, “9”,or “10”, wherein “0” means that there was no or little difference in thedegree of germination or growth between the treated plants and theuntreated plants at the time of evaluation, and “10” means that the testplants died completely or their germination or growth was completelyinhibited.

TEST EXAMPLE 1

Plastic pots each having an area of 25.5×17.3 cm² and a depth of 7 cmwere filled with upland soil, then seeded with corn (Zea mays), soybean(Glycine max), common lambsquarters (Chenopodium album), common ragweed(Ambrosia artemisiifolia) and pale smartweed (Polygonum lapathifolium).Then, in a greenhouse, corn was grown for 20 days; soybean and palesmartweed were grown for 25 days; and common lambsquarters and commonragweed were grown for 30 days.

A cinidon-ethyl emulsifiable concentrate obtained by mixing welltogether 10 parts of cinidon-ethyl, 14 parts of polyoxyethylenestyrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 partsof xylene and 35 parts of cyclohexanone, a formulated bentazone product(trade name: Basagran; manufacturer, BASF AG) and a mixture of saidcinidon-ethyl emulsifiable concentrate and said formulated bentazoneproduct were independently diluted in their prescribed amounts withwater, and then uniformly sprayed over the test plants with a smallsprayer. After the application, the test plants were grown in thegreenhouse for 20 days, and the herbicidal activity was then examined.The results are given in Table 1. The marks in the table are defined asfollows.

T: Corn, D: Soybean, S: Common lambsquarters,

B: Common ragweed, P: Pale smartweed

TABLE 1 crop phy- Herbicidal Examined Dosage totoxicity activityCompound (g/ha) T D S B P Cinidon-ethyl  10 2 3 2 4 1 bentazone 280 0 02 3 4 Cinidon-ethyl +  10 + 2 3 8 9 8 bentazone 280

Effect of the invention

A wide variety of weeds in corn fields, soybean fields, wheat fields,barley fields, oats fields, rye fields, rice fields, paddy fields or thelike, can be controlled with selectivity by using the present inventivecomposition.

What is claimed is:
 1. A synergistic herbicidal composition comprising(i) 3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide, and (ii)ethyl2-chloro-3-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindolin-2-yl)phenyl]acrylateas active ingredients.
 2. The herbicidal composition according to claim1, wherein the weight ratio of component (i) to component (ii) in saidcomposition is from about 4:1 to 400:1.
 3. A method for controllingweeds, which comprises applying a synergistically herbicidally effectiveamount of (i) 3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one2,2-dioxide, and (ii) ethyl2-chloro-3-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindolin-2-yl)phenyl]acrylateto said weeds.
 4. The method for controlling weeds according to claim 3,wherein the weight ratio of component (i) to component (ii) beingapplied to said weeds is from about 4:1 to 400:1.
 5. The method forcontrolling weeds according to claim 3 or 4, a total amount ofcomponents (i) and (ii) being applied to said weeds is from 50 to 5,000g per hectare.
 6. The method according to claim 3, wherein the weeds arethose growing in a corn field.
 7. The method according to claim 3,wherein the weeds are those growing in a soybean field.
 8. The methodaccording to claim 4, wherein the weeds are those growing in a cornfield.
 9. The method according to claim 5, wherein the weeds are thosegrowing in a corn field.
 10. The method according to claim 4, whereinthe weeds are those growing in a soybean field.
 11. The method accordingto claim 5, wherein the weeds are those growing in a soybean field. 12.The herbicidal composition according to claim 1, wherein the weightratio of component (i) to component (ii) in said composition is fromabout 4:1 to 40:1.
 13. The method for controlling weeds according toclaim 3, wherein weight ratio of component (i) to component (ii) in saidcomposition is from about 4:1 to 40:1.